반응 #74375

반응 방정식

1-bromocyclopentane-carboxylic acid

oxalyl chloride

N,N-diisopropylethylamine

→

title compound

Ethyl 1-bromocyclopentanecarboxylate

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타After removing the low-boiling solvents in vacuo, ethanol (50 mL)
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   workup.STIRRINGThe mixture was stirred at ambient temperature for 20 min
4. 4
   기타After removing the low-boiling solvents in vacuo
5. 5
   기타the residue was partitioned between diethyl ether and water
6. 6
   세척The organic portion was washed with water and brine
7. 7
   여과The crude product was filtered through a plug of silica gel using 0 to 10% EtOAc in hexanes as the eluant

실험 절차

DMF (a few drops) was added to a mixture of 1-bromocyclopentane-carboxylic acid (23.9 g, 124 mmol) and oxalyl chloride (11.6 mL, 130 mmol) in 250 mL of CH2Cl2. The mixture was stirred at ambient temperature for 2 h. After removing the low-boiling solvents in vacuo, ethanol (50 mL) was added to the residue followed by the addition of N,N-diisopropylethylamine (22.7 mL, 130 mmol). The mixture was stirred at ambient temperature for 20 min. After removing the low-boiling solvents in vacuo, the residue was partitioned between diethyl ether and water. The organic portion was washed with water and brine, and conc. in vacuo. The crude product was filtered through a plug of silica gel using 0 to 10% EtOAc in hexanes as the eluant. The title compound was obtained as a pale oil.

출처